$212 Find Cheap Flights from Hawaii to Chicago - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Chicago departing on 9/4. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Flight Deals

Cheap Flights from Hawaii to Chicago

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Hawaii to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Hawaii to Chicago

Wed, Sep 23 - Wed, Sep 30
Delta Logo
9:54 pm - 6:01 pm
LIH
-
ORD
15h 07m
1 stop
Delta Logo
12:50 pm - 7:10 pm
ORD
-
LIH
11h 20m
1 stop
$424Delta
Thu, Sep 24 - Wed, Sep 30
Delta Logo
9:54 pm - 6:01 pm
LIH
-
ORD
15h 07m
1 stop
Delta Logo
6:00 am - 5:40 pm
ORD
-
LIH
16h 40m
2 stops
$430Delta
Wed, Sep 23 - Wed, Sep 30
American Airlines Logo
1:25 pm - 5:59 am
LIH
-
ORD
11h 34m
1 stop
American Airlines Logo
9:10 pm - 11:48 am
ORD
-
LIH
19h 38m
1 stop
$482American Airlines
Wed, Aug 12 - Mon, Aug 17
Multiple Airlines Logo
12:23 pm - 5:00 am
LIH
-
ORD
11h 37m
1 stop
Multiple Airlines Logo
7:59 pm - 11:28 am
ORD
-
LIH
20h 29m
1 stop
$494Multiple Airlines
Wed, Sep 23 - Wed, Sep 30
Multiple Airlines Logo
7:21 pm - 7:21 pm
LIH
-
ORD
19h 00m
2 stops
Multiple Airlines Logo
7:20 am - 5:03 pm
ORD
-
LIH
14h 43m
2 stops
$495Multiple Airlines
Thu, Aug 27 - Sun, Aug 30
Alaska Airlines Logo
10:35 am - 1:22 pm
KOA
-
ORD
21h 47m
1 stop
Alaska Airlines Logo
8:17 pm - 2:48 pm
ORD
-
KOA
23h 31m
1 stop
$533Alaska Airlines
Thu, Aug 13 - Tue, Aug 18
Southwest Logo
8:10 am - 4:30 am
HNL
-
MDW
15h 20m
1 stop
Southwest Logo
3:05 pm - 9:20 pm
MDW
-
HNL
11h 15m
1 stop
$554Southwest
Thu, Aug 13 - Tue, Aug 18
Southwest Logo
8:10 am - 4:30 am
HNL
-
MDW
15h 20m
1 stop
Southwest Logo
12:00 pm - 9:20 pm
MDW
-
HNL
14h 20m
2 stops
$560Southwest
Mon, Nov 2 - Tue, Nov 10
Alaska Airlines Logo
4:52 pm - 7:00 pm
KOA
-
ORD
22h 08m
2 stops
Alaska Airlines Logo
7:25 am - 3:52 pm
ORD
-
KOA
12h 27m
1 stop
$571Alaska Airlines
Fri, Dec 4 - Sat, Dec 12
American Airlines Logo
2:47 pm - 5:59 am
OGG
-
ORD
11h 12m
1 stop
American Airlines Logo
8:45 pm - 1:17 pm
ORD
-
OGG
20h 32m
1 stop
$612American Airlines
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$212
Best time to beat the crowds with an average 12% drop in price.
Most popular time to fly with an average 46% increase in price.
Flight from Lihue to Chicago O'Hare Airport

FAQs for booking flights from Hawaii to Chicago

  • How does KAYAK find such low prices on flights from Hawaii to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Hawaii to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Hawaii to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Hawaii is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Hawaii to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Hawaii with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Hawaii to Chicago?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Hawaii up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Saint Joseph
Hammond
Portage
Lansing
Valparaiso
Munster
Schererville
Chesterton
Porter
Monticello
Saint John
Griffith

Everything you need to know for your flight to Chicago

Cabin class types available on flights to Hawaii

Cabin classes available on flights to Chicago. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.
First Class flights to Chicagofrom $5,200
Business Class flights to Chicagofrom $3,805
Premium Economy Class flights to Chicagofrom $694
Economy Class flights to Chicagofrom $334